EFFICIENT ONE-POT SYNTHESIS OF BENZO[e]PYRAZOLO-[1,5-c][1,3]THIAZINE DERIVATIVES UNDER COPPER-CATALYZED CONDITIONS

被引:6
|
作者
Jie, Jiyang [1 ]
Li, Haoyi [1 ]
Piao, Meihui [1 ]
Yang, Xiaobo [1 ]
机构
[1] Shenyang Normal Univ, Coll Chem & Chem Engn, Shenyang 110034, Liaoning, Peoples R China
基金
中国国家自然科学基金;
关键词
Copper Catalyst; One-Pot Reaction; S-Arylation Reaction; Pyrazole; Thiazine; DIRECT IMINE ACYLATION; HETEROCYCLIC SCAFFOLDS; ACID-DERIVATIVES; CYCLIZATION; SCOPE;
D O I
10.3987/COM-16-13477
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient method has been developed for the synthesis of benzo[e]pyrazolo[1,5-c][1,3]thiazines via one-pot two-step reactions of readily available substituted 1-(2-halopheny1)-3-akylprop-2-yn-1-ones, hydrazine hydrochloride and beta-oxodithioesters under mild conditions, and the corresponding benzo[e]pyrazolo[1,5-c][1,3]thiazines were obtained in good to excellent yields. The novel method affords a new strategy for the construction of diverse and useful poly N, S-heterocyclic compounds.
引用
收藏
页码:1215 / 1223
页数:9
相关论文
共 50 条
  • [1] Dual Roles of β-Oxodithioesters in the Copper-Catalyzed Synthesis of Benzo[e]pyrazolo[1,5-c][1,3]thiazine Derivatives
    Wen, Li-Rong
    Yuan, Wen-Kui
    Li, Ming
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (10) : 4942 - 4949
  • [2] Cu-Catalyzed Synthesis of Novel Benzo[e]pyrazolo[1,5-c][1,3]thiazine Derivatives
    Li, Ming
    Zhang, Jianwei
    Wen, Lirong
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2014, 34 (12) : 2478 - 2486
  • [3] An Efficient One-Pot Synthesis of Benzo[1,4]Thiazines, Benzo[1,3]Thiazoles and Benzo[1,5] Thiazepines
    El-Mahdy, Ahmed F. M.
    Mohamed, Omima S.
    El-Sherief, Hassan A. H.
    Hozien, Zeinab A.
    CURRENT ORGANIC SYNTHESIS, 2017, 14 (04) : 604 - 611
  • [4] Copper-catalyzed one-pot synthesis of 1,4-benzothiazine-3-ones
    Zhang, Lingyu
    Zhang, Songlin
    TETRAHEDRON LETTERS, 2023, 130
  • [5] One-pot synthesis of novel pyrazolo[4,3-e][1,2,4]triazolo[1,5-c] pyrimidines under microwave irradiation in a green solvent
    Ng, Jia Hui
    Dolzhenko, Anton, V
    TETRAHEDRON, 2023, 141
  • [6] Copper-Catalyzed One-Pot Synthesis of α-Ketoamides from 1-Arylethanols
    Sharma, Nidhi
    Kotha, Surya Srinivas
    Lahiri, Nabajit
    Sekar, Govindasamy
    SYNTHESIS-STUTTGART, 2015, 47 (05): : 726 - 736
  • [7] One-Pot Synthesis of Benzo[d][1,3]selenazole Derivatives by Using Carbon-Supported Copper Catalyst
    Zhou, Meiyun
    Wu, Zhaojun
    Li, Yiquan
    Zheng, Wenjie
    Ji, Shengbin
    Zhou, Hua
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2015, 35 (06) : 1270 - 1275
  • [8] One-Pot Synthesis of Pyrrolo[1,2-a]quinoxaline Derivatives through Copper-Catalyzed Cascade Reactions
    Jiang, Zengqiang
    Zhang, Jie
    Tong, Yao
    Shi, Xuesong
    Miao, Dazhuang
    Han, Shiqing
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2014, 34 (09) : 1845 - 1850
  • [9] Synthesis of Chrysene Derivatives via Copper-Catalyzed One-Pot Dimerization of 2-Alkynyl-1-acetylbenzenes
    Guo, Biao
    Zheng, Liyao
    Yang, Lichen
    Hua, Ruimao
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (10) : 4352 - 4357
  • [10] Facile and Efficient Synthesis of a New Class of Pyrazolo[1,5-a]Pyrimidine Derivatives Via One-Pot Multicomponent Reactions
    A. El-Mekabaty
    A. M. Hasel
    Chemistry of Heterocyclic Compounds, 2015, 50 : 1608 - 1615